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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 23:03:50 UTC

Update Date

2021-09-26 22:54:50 UTC

HMDB ID

HMDB0246020

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol

Description

3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol, also known as 3,4-DHPG or 1-((3-hydroxy-4-methoxy)-1-naphthoxy)-2,3-propanediol, belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position. Based on a literature review a significant number of articles have been published on 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol. This compound has been identified in human blood as reported by (PMID: 31557052 ). 3-(3-hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0246020
     RDKit          3D
3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol
 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.0317    2.0822    0.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4910    1.0056    1.2054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2349    0.4825    0.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1059    0.9817    1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2206    2.0302    2.4399 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1591    0.4694    1.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3338   -0.5635    0.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5251   -1.0973    0.0535 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8315   -1.0091    0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6081    0.2072   -0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1954    1.3678    0.5336 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7144    0.3961   -1.5710 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6263    1.3920   -1.8856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8462   -1.0633   -0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7466   -2.0955   -1.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8670   -2.6331   -1.7972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1160   -2.0966   -1.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2209   -1.0575   -0.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0838   -0.5540    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8571    1.6764   -0.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2222    2.5224   -0.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4670    2.8590    1.1059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4055    2.4155    2.8986 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9708    0.9196    1.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9888   -1.1580    1.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3557   -1.9305   -0.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6803    0.0361    0.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3394    1.2583    1.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0694   -0.5391   -2.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7484    0.6593   -2.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4939    2.1497   -1.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2216   -2.4929   -1.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7799   -3.4305   -2.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9627   -2.5172   -1.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2029   -0.6728   -0.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  7 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19  3  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  6 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
M  END

  Mrv1652309112101042D          

 19 20  0  0  0  0            999 V2000
   -4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
  3 12  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 15 18  1  0  0  0  0
  4 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0246020

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C(OCC(O)CO)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O5/c1-18-14-11-5-3-2-4-10(11)13(6-12(14)17)19-8-9(16)7-15/h2-6,9,15-17H,7-8H2,1H3

> <INCHI_KEY>
JBWCTTBDNCDIEV-UHFFFAOYSA-N

> <FORMULA>
C14H16O5

> <MOLECULAR_WEIGHT>
264.277

> <EXACT_MASS>
264.099773615

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.232047713378854

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(3-hydroxy-4-methoxynaphthalen-1-yl)oxy]propane-1,2-diol

> <ALOGPS_LOGP>
0.69

> <JCHEM_LOGP>
1.023377765666666

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.624319379789632

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.67107942223681

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9686166758417567

> <JCHEM_POLAR_SURFACE_AREA>
79.15

> <JCHEM_REFRACTIVITY>
69.67030000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.49e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(3-hydroxy-4-methoxynaphthalen-1-yl)oxy]propane-1,2-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0246020
     RDKit          3D
3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol
 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.0317    2.0822    0.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4910    1.0056    1.2054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2349    0.4825    0.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1059    0.9817    1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2206    2.0302    2.4399 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1591    0.4694    1.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3338   -0.5635    0.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5251   -1.0973    0.0535 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8315   -1.0091    0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6081    0.2072   -0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1954    1.3678    0.5336 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7144    0.3961   -1.5710 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6263    1.3920   -1.8856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8462   -1.0633   -0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7466   -2.0955   -1.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8670   -2.6331   -1.7972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1160   -2.0966   -1.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2209   -1.0575   -0.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0838   -0.5540    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8571    1.6764   -0.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2222    2.5224   -0.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4670    2.8590    1.1059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4055    2.4155    2.8986 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9708    0.9196    1.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9888   -1.1580    1.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3557   -1.9305   -0.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6803    0.0361    0.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3394    1.2583    1.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0694   -0.5391   -2.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7484    0.6593   -2.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4939    2.1497   -1.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2216   -2.4929   -1.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7799   -3.4305   -2.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9627   -2.5172   -1.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2029   -0.6728   -0.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  7 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19  3  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  6 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0      -8.002  -6.160   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -8.002  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -6.668  -3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       0.000  -0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -8.002  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5   19                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7    3                                                  
CONECT   13    6   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18   15                                                            
CONECT   19    4                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0246020
HETATM    1  C1  UNL     1      -4.032   2.082   0.460  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.491   1.006   1.205  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.235   0.483   0.920  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.106   0.982   1.524  1.00  0.00           C  
HETATM    5  O2  UNL     1      -1.221   2.030   2.440  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.159   0.469   1.249  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.334  -0.564   0.355  1.00  0.00           C  
HETATM    8  O3  UNL     1       1.525  -1.097   0.054  1.00  0.00           O  
HETATM    9  C6  UNL     1       2.831  -1.009   0.299  1.00  0.00           C  
HETATM   10  C7  UNL     1       3.608   0.207  -0.069  1.00  0.00           C  
HETATM   11  O4  UNL     1       3.195   1.368   0.534  1.00  0.00           O  
HETATM   12  C8  UNL     1       3.714   0.396  -1.571  1.00  0.00           C  
HETATM   13  O5  UNL     1       4.626   1.392  -1.886  1.00  0.00           O  
HETATM   14  C9  UNL     1      -0.846  -1.063  -0.257  1.00  0.00           C  
HETATM   15  C10 UNL     1      -0.747  -2.095  -1.160  1.00  0.00           C  
HETATM   16  C11 UNL     1      -1.867  -2.633  -1.797  1.00  0.00           C  
HETATM   17  C12 UNL     1      -3.116  -2.097  -1.498  1.00  0.00           C  
HETATM   18  C13 UNL     1      -3.221  -1.057  -0.589  1.00  0.00           C  
HETATM   19  C14 UNL     1      -2.084  -0.554   0.020  1.00  0.00           C  
HETATM   20  H1  UNL     1      -4.857   1.676  -0.162  1.00  0.00           H  
HETATM   21  H2  UNL     1      -3.222   2.522  -0.158  1.00  0.00           H  
HETATM   22  H3  UNL     1      -4.467   2.859   1.106  1.00  0.00           H  
HETATM   23  H4  UNL     1      -0.406   2.415   2.899  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.971   0.920   1.790  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.989  -1.158   1.428  1.00  0.00           H  
HETATM   26  H7  UNL     1       3.356  -1.930  -0.135  1.00  0.00           H  
HETATM   27  H8  UNL     1       4.680   0.036   0.262  1.00  0.00           H  
HETATM   28  H9  UNL     1       3.339   1.258   1.517  1.00  0.00           H  
HETATM   29  H10 UNL     1       4.069  -0.539  -2.051  1.00  0.00           H  
HETATM   30  H11 UNL     1       2.748   0.659  -2.027  1.00  0.00           H  
HETATM   31  H12 UNL     1       4.494   2.150  -1.247  1.00  0.00           H  
HETATM   32  H13 UNL     1       0.222  -2.493  -1.376  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.780  -3.430  -2.494  1.00  0.00           H  
HETATM   34  H15 UNL     1      -3.963  -2.517  -1.992  1.00  0.00           H  
HETATM   35  H16 UNL     1      -4.203  -0.673  -0.387  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5    6
CONECT    5   23
CONECT    6    7    7   24
CONECT    7    8   14
CONECT    8    9
CONECT    9   10   25   26
CONECT   10   11   12   27
CONECT   11   28
CONECT   12   13   29   30
CONECT   13   31
CONECT   14   15   15   19
CONECT   15   16   32
CONECT   16   17   17   33
CONECT   17   18   34
CONECT   18   19   19   35
END

HMDB0246020
     RDKit          3D
3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol
 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.0317    2.0822    0.4596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4910    1.0056    1.2054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2349    0.4825    0.9196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1059    0.9817    1.5243 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2206    2.0302    2.4399 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1591    0.4694    1.2494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3338   -0.5635    0.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5251   -1.0973    0.0535 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8315   -1.0091    0.2991 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6081    0.2072   -0.0688 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1954    1.3678    0.5336 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7144    0.3961   -1.5710 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6263    1.3920   -1.8856 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8462   -1.0633   -0.2569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7466   -2.0955   -1.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8670   -2.6331   -1.7972 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1160   -2.0966   -1.4979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2209   -1.0575   -0.5893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0838   -0.5540    0.0198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8571    1.6764   -0.1617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2222    2.5224   -0.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4670    2.8590    1.1059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4055    2.4155    2.8986 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9708    0.9196    1.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9888   -1.1580    1.4277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3557   -1.9305   -0.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6803    0.0361    0.2622 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3394    1.2583    1.5172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0694   -0.5391   -2.0514 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7484    0.6593   -2.0275 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4939    2.1497   -1.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2216   -2.4929   -1.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7799   -3.4305   -2.4935 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9627   -2.5172   -1.9922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2029   -0.6728   -0.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  7 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19  3  1  0
 19 14  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  5 23  1  0
  6 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
 18 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3,4-DHPG	MeSH
1-((3-Hydroxy-4-methoxy)-1-naphthoxy)-2,3-propanediol	MeSH

Chemical Formula

C₁₄H₁₆O₅

Average Molecular Weight

264.277

Monoisotopic Molecular Weight

264.099773615

IUPAC Name

3-[(3-hydroxy-4-methoxynaphthalen-1-yl)oxy]propane-1,2-diol

Traditional Name

3-[(3-hydroxy-4-methoxynaphthalen-1-yl)oxy]propane-1,2-diol

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(OCC(O)CO)C2=CC=CC=C12

InChI Identifier

InChI=1S/C14H16O5/c1-18-14-11-5-3-2-4-10(11)13(6-12(14)17)19-8-9(16)7-15/h2-6,9,15-17H,7-8H2,1H3

InChI Key

JBWCTTBDNCDIEV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthols and derivatives

Direct Parent

Naphthols and derivatives

Alternative Parents

Substituents

2-naphthol
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Secondary alcohol
1,2-diol
Ether
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.69	ALOGPS
logP	1.02	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.67	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	79.15 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	69.67 m³·mol⁻¹	ChemAxon
Polarizability	27.23 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	190.032	30932474
DeepCCS	[M+Na]+	165.597	30932474
AllCCS	[M+H]+	160.5	32859911
AllCCS	[M+H-H2O]+	157.0	32859911
AllCCS	[M+NH4]+	163.9	32859911
AllCCS	[M+Na]+	164.8	32859911
AllCCS	[M-H]-	162.2	32859911
AllCCS	[M+Na-2H]-	162.1	32859911
AllCCS	[M+HCOO]-	162.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol	COC1=C(O)C=C(OCC(O)CO)C2=CC=CC=C12	3608.8	Standard polar	33892256
3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol	COC1=C(O)C=C(OCC(O)CO)C2=CC=CC=C12	2381.7	Standard non polar	33892256
3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol	COC1=C(O)C=C(OCC(O)CO)C2=CC=CC=C12	2429.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol GC-MS (Non-derivatized) - 70eV, Positive	splash10-01qc-9560000000-f1fd929b1c92bb7f7d98	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol GC-MS (TBDMS_3_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol 10V, Positive-QTOF	splash10-0006-0910000000-9d11533c112dab62a4db	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol 20V, Positive-QTOF	splash10-0006-0900000000-000f76fa0c4c509ba980	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol 40V, Positive-QTOF	splash10-002r-2900000000-c1461f38b5711e0592d3	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol 10V, Negative-QTOF	splash10-000i-0920000000-35dbf4138ff3494afb84	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol 20V, Negative-QTOF	splash10-00dr-0900000000-d0a7399fb5440ab7b083	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol 40V, Negative-QTOF	splash10-00di-0900000000-5473bbbd595cc8fc7abf	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

115644

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

130755

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol (HMDB0246020)

MOL for HMDB0246020 (3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol)

3D MOL for HMDB0246020 (3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol)

3D SDF for HMDB0246020 (3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol)

3D-SDF for HMDB0246020 (3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol)

PDB for HMDB0246020 (3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol)

3D PDB for HMDB0246020 (3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol)

SMILES for HMDB0246020 (3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol)

INCHI for HMDB0246020 (3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol)

Structure for HMDB0246020 (3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol)

3D Structure for HMDB0246020 (3-(3-Hydroxy-4-methoxynaphthalen-1-yl)oxypropane-1,2-diol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra